CA1143095A - Resines durcissables derivees de lactone - Google Patents

Resines durcissables derivees de lactone

Info

Publication number: CA1143095A
Authority: CA; Canada
Prior art keywords: lactone; percent; resin; isocyanate; derived
Prior art date: 1978-10-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000335005A

Other languages

English (en)

Inventor

Wen-Hsuan Chang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PPG Industries Ohio Inc

Original Assignee

PPG Industries Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-10-06

Filing date

1979-09-04

Publication date

1983-03-15

1979-09-04 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1983-03-15 Application granted granted Critical

1983-03-15 Publication of CA1143095A publication Critical patent/CA1143095A/fr

Status Expired legal-status Critical Current

Links

150000002596 lactones Chemical class 0.000 title claims abstract description 56
229920005989 resin Polymers 0.000 title claims abstract description 48
239000011347 resin Substances 0.000 title claims abstract description 48
-1 acrylyl Chemical group 0.000 claims abstract description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
150000002148 esters Chemical class 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000012948 isocyanate Substances 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
150000002513 isocyanates Chemical class 0.000 claims abstract description 16
239000007795 chemical reaction product Substances 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 18
229920005862 polyol Polymers 0.000 claims description 17
150000003077 polyols Chemical class 0.000 claims description 17
239000000047 product Substances 0.000 claims description 15
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 13
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 13
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
239000004593 Epoxy Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
125000005442 diisocyanate group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 4
238000000576 coating method Methods 0.000 abstract description 22
238000005299 abrasion Methods 0.000 abstract description 4
239000011248 coating agent Substances 0.000 description 13
239000008199 coating composition Substances 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000000758 substrate Substances 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 7
239000000376 reactant Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
229940063559 methacrylic acid Drugs 0.000 description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000012975 dibutyltin dilaurate Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
239000012190 activator Substances 0.000 description 2
238000007792 addition Methods 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000011084 recovery Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229940113165 trimethylolpropane Drugs 0.000 description 2
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
BOOBDAVNHSOIDB-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC(C(=O)OOC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl BOOBDAVNHSOIDB-UHFFFAOYSA-N 0.000 description 1
SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
CHBDDJMPIAJNFA-UHFFFAOYSA-N 1,1-diisocyanatotridecane Chemical compound CCCCCCCCCCCCC(N=C=O)N=C=O CHBDDJMPIAJNFA-UHFFFAOYSA-N 0.000 description 1
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
PQDIQKXGPYOGDI-UHFFFAOYSA-N 1,3,5-triisocyanatobenzene Chemical compound O=C=NC1=CC(N=C=O)=CC(N=C=O)=C1 PQDIQKXGPYOGDI-UHFFFAOYSA-N 0.000 description 1
DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
229940043375 1,5-pentanediol Drugs 0.000 description 1
NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
RQAVSDINDRNIKL-UHFFFAOYSA-N 1-chloro-3-isocyanatopropane Chemical compound ClCCCN=C=O RQAVSDINDRNIKL-UHFFFAOYSA-N 0.000 description 1
LZTQRHXMOGHIET-UHFFFAOYSA-N 1-chloro-4-(3-isocyanatopropoxy)butane Chemical compound ClCCCCOCCCN=C=O LZTQRHXMOGHIET-UHFFFAOYSA-N 0.000 description 1
ZUQBWPZNPMMWQK-UHFFFAOYSA-N 1-chloro-4-isocyanatocyclohexane Chemical compound ClC1CCC(N=C=O)CC1 ZUQBWPZNPMMWQK-UHFFFAOYSA-N 0.000 description 1
ZVFNUQWYLXXSJM-UHFFFAOYSA-N 1-ethyl-2-isocyanatobenzene Chemical compound CCC1=CC=CC=C1N=C=O ZVFNUQWYLXXSJM-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
WVRHNZGZWMKMNE-UHFFFAOYSA-N 2-hydroxy-1-[2-(2-methylpropyl)phenyl]-2-phenylethanone Chemical compound CC(C)CC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 WVRHNZGZWMKMNE-UHFFFAOYSA-N 0.000 description 1
IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
ZWMJUBVSXUPLKD-UHFFFAOYSA-N 2-hydroxypentyl 2-methylprop-2-enoate Chemical compound CCCC(O)COC(=O)C(C)=C ZWMJUBVSXUPLKD-UHFFFAOYSA-N 0.000 description 1
GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
FZYJCVMLEDZTJW-UHFFFAOYSA-N 3-hydroxypentyl prop-2-enoate Chemical compound CCC(O)CCOC(=O)C=C FZYJCVMLEDZTJW-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
IZOOKIPOZQWSGC-UHFFFAOYSA-N 5-hydroxydecyl 2-methylprop-2-enoate Chemical compound CCCCCC(O)CCCCOC(=O)C(C)=C IZOOKIPOZQWSGC-UHFFFAOYSA-N 0.000 description 1
YGTVWCBFJAVSMS-UHFFFAOYSA-N 5-hydroxypentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCO YGTVWCBFJAVSMS-UHFFFAOYSA-N 0.000 description 1
IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical class OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
YROVIFKSHZGNSF-UHFFFAOYSA-N 6-hydroxynonyl prop-2-enoate Chemical compound CCCC(O)CCCCCOC(=O)C=C YROVIFKSHZGNSF-UHFFFAOYSA-N 0.000 description 1
CPDZIKHNXVPGST-UHFFFAOYSA-N 7-hydroxyheptyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCO CPDZIKHNXVPGST-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910010293 ceramic material Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
239000011094 fiberboard Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
239000000123 paper Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
239000003504 photosensitizing agent Substances 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000005507 spraying Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/6725—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing ester groups other than acrylate or alkylacrylate ester groups
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/92—Polyurethane having terminal ethylenic unsaturation

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Macromonomer-Based Addition Polymer (AREA)
Polyurethanes Or Polyureas (AREA)
Polymerisation Methods In General (AREA)
Paints Or Removers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000335005A 1978-10-06 1979-09-04 Resines durcissables derivees de lactone Expired CA1143095A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US949,181		1978-10-06
US05/949,181 US4188472A (en)	1978-10-06	1978-10-06	Curable lactone derived resins

Publications (1)

Publication Number	Publication Date
CA1143095A true CA1143095A (fr)	1983-03-15

Family

ID=25488706

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000335005A Expired CA1143095A (fr)	1978-10-06	1979-09-04	Resines durcissables derivees de lactone

Country Status (7)

Country	Link
US (1)	US4188472A (fr)
JP (1)	JPS5550011A (fr)
CA (1)	CA1143095A (fr)
DE (1)	DE2939584A1 (fr)
FR (1)	FR2438060A1 (fr)
GB (1)	GB2032446B (fr)
IT (1)	IT1121046B (fr)

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US4264757A (en) *	1979-06-26	1981-04-28	Union Carbide Corporation	Radiation-curable allyl- or vinyl capped polycaprolactone compositions
DE3217653C2 (de) *	1981-05-11	1995-05-18	Daicel Chem	Verfahren zur Herstellung eines epsilon-Caprolacton-modifizierten Vinylmonomeren und dessen Verwendung zur Herstellung eines Mischpolymerisates
CA1237239A (fr) *	1982-11-02	1988-05-24	Joseph V. Koleske	Compositions a teneur de monomere reactif derive du lactone
US4504635A (en) *	1982-11-02	1985-03-12	Union Carbide Corporation	Process for the preparation of polymeric compositions
US4683287A (en) *	1982-11-02	1987-07-28	Union Carbide Corporation	Compositions containing a reactive monomer derived from a lactone
CA1246290A (fr) *	1983-06-30	1988-12-06	Claiborn L. Osborn	Compositions de polyol, d'isocyanate et d'un produit d'addition lactone-acrylate, comme revetements reticulables
US4618635A (en) *	1983-06-30	1986-10-21	Union Carbide Corporation	Coating compositions prepared from lactone-acrylate adduct, polyol and isocyanate
US4585702A (en) *	1983-06-30	1986-04-29	Union Carbide Corporation	Magnetic recording medium
US4725653A (en) *	1983-10-27	1988-02-16	Union Carbide Corporation	Low viscosity adducts of a polycaprolactone polyol and a polyepoxide
JPS6121119A (ja) *	1984-07-10	1986-01-29	Yokohama Rubber Co Ltd:The	光硬化型樹脂組成物
JPS6121118A (ja) *	1984-07-10	1986-01-29	Yokohama Rubber Co Ltd:The	光硬化型樹脂組成物
CA1238446A (fr) *	1984-08-09	1988-06-21	Union Carbide Corporation	Liants souples autoreticulateurs
US4560494A (en) *	1984-12-27	1985-12-24	The Sherwin-Williams Company	Isocyanate functional prepolymers and coating materials based thereon
US4619955A (en) *	1984-12-27	1986-10-28	The Sherwin-Williams Company	Isocyanate functional urethanes as flexibilizing additives in coating vehicles
US4874799A (en) *	1985-05-17	1989-10-17	M&T Chemicals Inc.	Aqueous akaline developable, UV curable urethane acrylate compounds and compositions useful for forming liquid 100 percent solids, solvent-free solder mask coatings
EP0219710A1 (fr) *	1985-09-25	1987-04-29	Union Carbide Corporation	Liants flexibles autoréticulants
US4680361A (en) *	1986-02-20	1987-07-14	Union Carbide Corporation	Novel polymers and crosslinked compositions made therefrom
US4786749A (en) *	1986-02-20	1988-11-22	Union Carbide Corporation	Carboxyl-terminated lactone acrylates
US4983689A (en) *	1987-05-07	1991-01-08	Yu Simon H	Process for making macromolecular monomers of polylactones with terminal acryloyl unsaturation and block copolymers thereof
US4847329A (en) *	1987-06-30	1989-07-11	Union Carbide Corporation	(N-substituted carbamoyloxy)alkanoyloxyalkyl acrylate polymers and compositions made therefrom
JPH0241380A (ja) *	1988-07-11	1990-02-09	Dent Inc	放射線硬化性塗料
US5616630A (en) *	1993-02-05	1997-04-01	Lord Corporation	Ester/urethane acrylate hybrid oligomers
WO1995011927A1 (fr) *	1993-10-26	1995-05-04	Lord Corporation	Oligomeres polydiene/acrylourethanne modifies par un polyester
AU6547496A (en) *	1995-07-28	1997-02-26	Henkel Corporation	Polyester oligomer acrylates
US5703141A (en) *	1995-09-25	1997-12-30	Tarkett Ag	UV curable coatings
AU1383699A (en) *	1997-11-06	1999-05-31	Edgington Company, The	Coating composition
CA2346675A1 (fr) *	1998-10-08	2000-04-13	Kaneka Corporation	Polymeres et compositions durcissables
KR20010093274A (ko) *	1999-11-30	2001-10-27	고지마 아끼로, 오가와 다이스께	저락톤변성 반응성 단량체 조성물, 이것을 사용한아크릴폴리올수지, 및 경화성 수지 조성물 및 도료 조성물
US6534128B1 (en)	2000-11-09	2003-03-18	3M Innovative Properties Company	Inks and other compositions incorporating low viscosity, radiation curable, polyester urethane oligomer
DE10318017A1 (de) *	2003-04-19	2004-11-04	Goldschmidt Ag	Neuartige Polyestersiloxanacrylate, deren Verwendung als Additive in strahlenhärtbaren Beschichtungen und Druckfarben und Verfahren zu deren Herstellung
US7294656B2 (en) *	2004-01-09	2007-11-13	Bayer Materialscience Llc	UV curable coating composition
US8576162B2 (en) *	2005-03-14	2013-11-05	Sipix Imaging, Inc.	Manufacturing processes of backplane for segment displays
US7956098B2 (en) *	2005-04-12	2011-06-07	Bayer Materialscience Llc	Coating compositions containing ethylenically unsaturated polyurethanes as binders
US7807753B2 (en) *	2005-06-23	2010-10-05	Nissan Motor Co., Ltd.	Coating composition and multilayered coating film forming method and coated article using this coating
US20060293484A1 (en) *	2005-06-24	2006-12-28	Bayer Materialscience Llc	Low viscosity, ethylenically-unsaturated polyurethanes
US8105746B2 (en) *	2006-02-17	2012-01-31	Kuraray Co., Ltd.	Tertiary alcohol derivative, polymer compound and photoresist composition
DE102006012274A1 (de) †	2006-03-15	2007-09-20	Votteler Lackfabrik Gmbh & Co. Kg	Lack zur Oberflächenbeschichtung von Formteilen
US9701802B2 (en) *	2009-04-08	2017-07-11	Allnex Ip S.A.R.L.	Reinforced UV-A curable composite compositions and methods
US20140275320A1 (en)	2013-03-14	2014-09-18	Allnex IP S.à.r.I.	Methods for making elastomers, elastomer compositions and related elastomers
US10100223B2 (en) *	2013-03-14	2018-10-16	Allnex Netherlands B.V.	Methods for making elastomers, elastomer compositions and related elastomers
US9738597B2 (en) *	2013-05-27	2017-08-22	Basf Se	Method for preparing urethane (meth)acrylates
KR20160011637A (ko) *	2013-05-27	2016-02-01	바스프 에스이	우레탄（메트）아크릴레이트의 제조 방법
WO2020131185A2 (fr)	2018-09-26	2020-06-25	Dvorchak Enterprises Llc	Compositions durcissables par uv à un composant et leurs procédés de fabrication

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US3186971A (en) *	1956-04-13	1965-06-01	Union Carbide Corp	Polyurethane polymers from lactone polyesters
US3169945A (en) *	1956-04-13	1965-02-16	Union Carbide Corp	Lactone polyesters
US3051687A (en) *	1957-04-30	1962-08-28	Union Carbide Corp	Polyurethane resins
US3509102A (en) *	1963-06-24	1970-04-28	Union Carbide Corp	Elastic fibers prepared from epsilon-caprolactone-based diol,an organic diisocyanate,and a diamine
US3651021A (en) *	1968-05-03	1972-03-21	Union Carbide Corp	Ethylenically unsaturated polylactone-based polyurethane elastomer and vulcanizates therefrom
US3654347A (en) *	1968-05-03	1972-04-04	Union Carbide Corp	Ethylenically unsaturated hydroxy-containing lactone products
GB1257638A (fr) *	1968-11-20	1971-12-22
US3700643A (en)	1970-09-02	1972-10-24	Union Carbide Corp	Radiation-curable acrylate-capped polycaprolactone compositions
GB1408141A (en) *	1971-12-09	1975-10-01	Laporte Ind	Polymeric compositions
US3931117A (en) *	1974-08-01	1976-01-06	Cook Paint And Varnish Company	Coating powders for protective films based on ε-caprolactam-blocked isocyanates
JPS5218222A (en) *	1975-08-04	1977-02-10	Tsurukichi Sakuma	Fluid joint
GB1564296A (en) *	1975-09-30	1980-04-02	Mobil Oil Corp	Radiation curable coating compositions

1978
- 1978-10-06 US US05/949,181 patent/US4188472A/en not_active Expired - Lifetime
1979
- 1979-09-04 CA CA000335005A patent/CA1143095A/fr not_active Expired
- 1979-09-27 JP JP12468379A patent/JPS5550011A/ja active Granted
- 1979-09-28 FR FR7924351A patent/FR2438060A1/fr not_active Withdrawn
- 1979-09-29 DE DE19792939584 patent/DE2939584A1/de not_active Withdrawn
- 1979-10-05 IT IT68939/79A patent/IT1121046B/it active
- 1979-10-05 GB GB7934581A patent/GB2032446B/en not_active Expired

Also Published As

Publication number	Publication date
IT7968939A0 (it)	1979-10-05
GB2032446B (en)	1982-11-24
DE2939584A1 (de)	1980-04-10
IT1121046B (it)	1986-03-26
JPS5733287B2 (fr)	1982-07-16
JPS5550011A (en)	1980-04-11
US4188472A (en)	1980-02-12
GB2032446A (en)	1980-05-08
FR2438060A1 (fr)	1980-04-30

Legal Events

Date	Code	Title	Description
2000-03-15	MKEX	Expiry

Publication	Publication Date	Title
CA1143095A (fr)	1983-03-15	Resines durcissables derivees de lactone
US4003751A (en)	1977-01-18	Coating and ink compositions
US5047261A (en)	1991-09-10	Process for the manufacture of coatings by radiocrosslinking
CA2271845C (fr)	2003-10-07	Oligomere multifonctionnel de polyacrylate et de polyurethane, procede de preparation et produits et polymeres traites correspondants
EP0021825B1 (fr)	1984-09-26	Uréthanes à base de polyol de polycaprolactone et procédés pour leur préparation
JP2000154230A (ja)	2000-06-06	新規なウレタンアクリレ―トおよび被覆組成物におけるその使用
EP1529793A2 (fr)	2005-05-11	Résine de polyisocyanate blocqué ayant des fonctions d'acrylate pour revêtements thermodurcissables ou durcissables par UV
CA1179444A (fr)	1984-12-11	Urethane-acrylates et compositions derivees, durcissables a la lumiere
US4956198A (en)	1990-09-11	Ultraviolet-curable cationic vinyl ether polyurethane coating compositions
KR0131008B1 (ko)	1998-04-13	대오염성이 우수한 광경화형 수지 조성물 및 이의 제품
JPH06507923A (ja)	1994-09-08	カプロラクトンオリゴマーポリオールを含有する被覆材
JP4026240B2 (ja)	2007-12-26	フルオレン骨格を有するウレタン（メタ）アクリレート
CN101445585A (zh)	2009-06-03	烯键式不饱和多异氰酸酯加成化合物及其应用和制备方法
JP2017165948A (ja)	2017-09-21	ポリウレタン（メタ）アクリレート、組成物、硬化物
JP4017055B2 (ja)	2007-12-05	（メタ）アクリル酸エステル、これを用いた樹脂組成物
JPH11286531A (ja)	1999-10-19	非結晶性ウレタン（メタ）アクリレート及びその組成物
JP2849240B2 (ja)	1999-01-20	防曇組成物用の活性エネルギー線硬化型オリゴマー
USRE30212E (en)	1980-02-12	Coating and ink compositions
WO1997004881A1 (fr)	1997-02-13	Acrylates d'oligomeres de polyester
JP4017056B2 (ja)	2007-12-05	（メタ）アクリル酸エステル、これを用いた樹脂組成物
JP2004315570A (ja)	2004-11-11	ウレタン（メタ）アクリレート樹脂組成物
DE69032403T2 (de)	1999-03-04	Frei radikal vernetzbare zusammensetzungen
JP2017132991A (ja)	2017-08-03	ポリウレタン（メタ）アクリレート、組成物、硬化物
JP2017222741A (ja)	2017-12-21	ポリウレタン（メタ）アクリレート、及びその組成物、硬化物
JP2899818B2 (ja)	1999-06-02	ウレタンアクリレートオリゴマーの製造方法